"The Pool Shark" is a song written by Tom T. Hall and recorded by American country music artist Dave Dudley.
The song was Dave Dudley's twenty-first release on the country chart and his only number one.
[1] The song tells the story of a young traveling man and hard-luck gambler who stops at a roadside bar.
The pro eventually winning all the main protagonist's money -- $187 plus his ring -- and leaves in a Cadillac with a beautiful young woman ("a blonde built like the rest of that car").
In the end, the protagonist asks the waitress out; the conversations with her had been interspersed occasionally with the main story.